Azo dyestuffs containing a diazo component from the aniline series and coupling component from the triazolopyridine series

ABSTRACT

Triazolopyridine azo dyestuffs of the formula ##STR1## where one of the two radicals A and E is nitrogen and the other is a radical of the formula C--R 1 , where R 1  is unsubstituted or substituted C 1  -C 20  -alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted mercapto, 
     one of the two radicals R 2  and R 4  is cyano, carbamoyl, carboxyl or C 1  -C 4  -alkoxycarbonyl and the other is a radical of the formula D--N═N--, where D is the radical of a diazo component from the aniline series, 
     R 3  is unsubstituted or substituted C 1  -C 4  -alkyl or phenyl, and 
     R 5  is hydroxyl, mercapto, unsubstituted or substituted amino or the radical of a CH-acidic compound, 
     and their use for dyeing or printing textile materials are described.

This application is a 371 of PCT/EP94/02756 filed Aug. 19, 1994.

DESCRIPTION

The present invention relates to novel triazolopyridine azo dye-stuffs of the formula I ##STR2## where

A is nitrogen,

E is a radical of the formula C---R¹, where R¹ is C₁ -C₂₀ -alkyl, which is unsubstituted or substituted and can be interrupted by 1 to 4 ether oxygen atoms, or is unsubstituted or substituted phenyl, mercapto or unsubstituted or substituted C₁ -C₂₀ -alkylthio,

one of the two radicals R² and R⁴ is cyano, carbamoyl, carboxyl or C₁ -C₄ -alkoxycarbonyl and the other is a radical of the formula D--N═N--, where D is a radical of a diazo component from the aniline series,

R³ is C₁ -C₄ -alkyl which may also be interrupted by an ether oxygen atom, or phenyl and

R⁵ is hydroxyl, mercapto, the radical --NY¹ Y², where Y¹ and Y² are identical or different and independently of one another in each case are hydrogen or C₁ -C₄ -alkyl or, together with the nitrogen atom bonding them, are a 5- or 6-membered saturated heterocyclic radical, or the radical of a CH-acidic compound,

with the proviso that if R⁴ is the radical of the formula D--N═N--, the two radicals A and E can also be exchanged for one another,

and their use for dyeing or printing textile materials.

Phenylazo dyestuffs which contain a coupling component from the 1,2,4-triazolo[1,5-a]pyridine series have already been disclosed in DE-A-4 020 768. The phenylazo group is located in ring position 4 of the heterocyclic system. However, it has been shown that these dyestuffs still have deficiencies in their applicational properties.

It is an object of the present invention to provide novel azo dyestuffs containing a coupling component from the triazolopyridine series and a diazo component from the aniline series and which have a high fastness to dry heat setting and pleating, high brilliance and high dyeing power.

We have found that this object is achieved by the triazolopyridine azo dyestuffs of the formula I described in greater detail at the beginning.

The dyestuffs of the formula I can occur in two or more tautomeric forms, which are all covered by the patent claim. For example, the dyestuffs where R² ═D--N═N-- can occur, inter alia, in the following tautomeric forms: ##STR3##

If in formula I substituted C₁ -C₂ O-alkyl radicals occur, suitable substituents can be e.g. unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, carboxyl or C₁ -C₂₀ -alkoxycarbonyl whose alkyl chain may be interrupted by 1 to 4 ether oxygen atoms and can be substituted by phenyl or phenoxy. The alkyl radicals here as a rule have 1 or 2 substituents.

If in formula I alkyl radicals occur which are interrupted by ether oxygen atoms, those alkyl radicals are preferred which are interrupted by 1 or 2 ether oxygen atoms.

If in formula I substituted phenyl radicals occur, suitable substituents can be e.g. C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, in this case in particular chlorine or bromine, nitro, cyano or carboxyl. The phenyl radicals here as a rule have 1 to 3 substituents.

If R⁵ in formula I is a radical of a CH-acidic compound, this radical can be derived e.g. from nitromethane, nitroethane or from compounds of the formulae IV to IX ##STR4## where

X¹ is cyano, nitro, C₁ -C₄ -alkanoyl, benzoyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or halogen, C₁ -C₄ -alkylsulfonyl, phenylsulfonyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or halogen, carboxyl, C₁ -C₄ -alkoxycarbonyl, phenoxycarbonyl, carbamoyl, C₁ -C₄ -mono- or -dialkylcarbamoyl, phenylcarbamoyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or halogen, phenyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen or nitro, benzothiazol-2-yl, benzimidazol-2-yl, 5-phenyl-1,3,4-thiadiazol-2-yl or 2-hydroxy-quinoxalin-3-yl,

X² is C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy,

X³ is C₁ -C₄ -alkoxycarbonyl, phenylcarbamoyl or benzimidazol-2-yl,

X⁴ is hydrogen or C₁ -C₆ -alkyl,

X⁵ is hydrogen, C₁ -C₄ -alkyl or phenyl and

X⁶ is C₁ -C₄ -alkyl.

CH-acidic compounds of the formulae IV, V or VII may in particular be mentioned here, where

X¹ is cyano, acetyl, benzoyl, C₁ -C₄ -alkoxycarbonyl, phenoxycarbonyl, C₁ -C₂ -monoalkylcarbamoyl, phenylcarbamoyl, phenyl, benzimidazol-2-yl, benzothiazol-2-yl or 5-phenyl-1,3,4-thiadiazol-2-yl,

X² is C₁ -C₂ -alkoxy,

X³ is C₁ -C₂ -alkoxycarbonyl or phenylcarbamoyl and

X⁵ is methyl.

The radical D in the dyestuffs according to the invention is derived from a diazo component from the aniline series.

Suitable diazo components D--NH₂ correspond, for example, to the formula II ##STR5## where

L¹, L² and L³ are identical or different and independently of one another in each case are hydrogen, C₁ -C₁₃ -alkyl, C₁ -C₄ -alkoxy which is unsubstituted or substituted by C₁ -C₄ -alkoxy, halo-C₁ -C₄ -alkoxy, hydroxy-C₁ -C₄ -alkoxy or cyano-C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio which is unsubstituted or substituted by C₁ -C₄ -alkoxy or C₁ -C₄ -alkylthio, phenoxy, halogen, cyano, C₁ -C₄ -alkanoylamino, C₁ -C₄ -alkylsulfonylamino, the radical NY¹ Y², where Y¹ and Y² in each case have the abovementioned meanings, or L¹ and L² together are the radical of the formula O--C₂ H₄ --O.

The radicals R¹, R³, L¹, L² and L³ are e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.

The radicals R¹, L¹, L² and L³ are furthermore e.g. pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, heptyl, 1-ethylpentyl, octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl or isotridecyl (the above names isooctyl, isononyl, isodecyl and isotridecyl are trivial names and originate from the alcohols obtained by the oxo synthesis--cf. for this Ullmanns Enzyklopadie der technischen Chemie [Ullmann's Encyclopedia of Industrial Chemistry], 4th Edition, volume 7, pages 215 to 217, and also Volume 11, pages 435 and 436).

The radicals R¹ are furthermore e.g. tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 2- or 4-butoxybutyl, 4,8-dioxadecyl, 3,6,9-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl, 3,6,9,12-tetraoxatetradecyl, 2-carboxyethyl, 2-methoxycarbonylethyl, benzyl, 1- or 2-phenylethyl, 2-, 3,- or 4-methylbenzyl, 2-, 3- or 4-methoxybenzyl, 2-, 3- or 4-chlorobenzyl, 2-, 3- or 4-nitrobenzyl, 3-benzyloxypropyl, phenoxymethyl, 6-phenoxy-4-oxahexyl, 8-phenoxy-4-oxaoctyl, phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-nitrophenyl, 2-, 3- or 4-carboxylphenyl, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, pentylthio, isopentylthio, neopentylthio, tert-pentylthio, hexylthio, heptylthio, 1-ethylpentylthio, octylthio, isooctylthio, 2-ethylhexylthio, nonylthio, isononylthio, decylthio, isodecylthio, undecylthio, dodecylthio, tridecylthio, isotridecylthio, tetradecylthio, pentadecylthio, hexadecylthio, heptadecylthio, octadecylthio, nonadecylthio or eicosylthio.

The radicals R³ are furthermore e.g. methoxymethyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl.

The radicals R² are e.g. methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl or sec-butoxycarbonyl.

The radicals R⁵ are e.g., as are furthermore also the radicals L¹, L² and L³, amino, mono- or dimethylamino, mono- or diethylamino, mono- or dipropylamino, mono- or diisopropylamino, mono- or dibutylamino, pyrrolidino, piperidino, morpholino, piperazino or N-(C₁ -C₄ -alkyl)piperazino.

The radicals L¹, L² and R³ are furthermore e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 2-butoxyethoxy, 2- or 3-methoxypropoxy, 2- or 3-ethoxypropoxy, 2- or 3-propoxypropoxy, 2- or 3-butoxypropoxy, 2- or 4-methoxybutoxy, 2- or 4-ethoxybutoxy, 2- or 4-propoxybutoxy, 2- or 4-butoxybutoxy, 2-(2-chloroethoxy)ethoxy, 2-(2-hydroxyethoxy)ethoxy, 2-(2-cyanoethoxy)ethoxy, methylthio, ethylthio, propylthio, isopropylthio, butylthio, 2-methoxyethylthio, 2-methylthioethylthio, fluorine, chlorine, bromine, formylamino, acetylamino, propionylamino, butyrylamino, isobutyrylamino, methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino or butylsulfonylamino.

Preferred triazolopyridine azo dyestuffs of the formula I are those where one of the two radicals R² and R⁴ is cyano and the other is a radical of the formula D--N═N--, where D has the abovementioned meaning.

Preferred triazolopyridine azo dyestuffs of the formula I are those where R² is cyano.

Preferred triazolopyridine azo dyestuffs of the formula I are furthermore those where R⁵ is hydroxyl.

Preferred triazolopyridine azo dyestuffs of the formula I are furthermore those where R³ is C₁ -C₄ -alkyl, in particular methyl.

Preferred triazolopyridine azo dyestuffs of the formula I are furthermore those where R¹ is C₁ -C₁₃ -alkyl which may be interrupted by 1 or 2 ether oxygen atoms, or is C₁ -C₁₃ -alkylthio.

Preferred triazolopyridine azo dyestuffs of the formula I are furthermore those where D--N═N-- is the radical of the formula ##STR6## where L¹, L² and L³ independently of one another in each case are hydrogen, C₁ -C₁₃ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₂ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen, or L¹ and L² together are the radical of the formula O--C₂ H₄ --O.

Particularly preferred triazolopyridine azo dyestuffs of the formula I are those where D--N═N-- is the radical of the formula ##STR7## where L¹ and L² independently of one another in each case are hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-C₂ -C₄ -alkoxy.

The triazolopyridine azo dyestuffs of the formula I according to the invention can be prepared by methods known per se. For example, a diazo component of the formula II can be diazotized in a manner known per se and coupled with a coupling component of the formula IIIa or IIIb ##STR8## where one of the two radicals Q¹ and Q² is hydrogen and the other is cyano, carbamoyl, carboxyl or C₁ -C₄ -alkoxycarbonyl and Q³ is cyano, carbamoyl, carboxyl or C₁ -C₄ -alkoxycarbonyl and R¹ and R⁵ in each case have the abovementioned meanings.

The coupling components of the formulae IIIa and IIIb are known per se and are described e.g. in the earlier German Patent Application P 43 26 758.0 or in U.S. Pat. No. 5,101,028.

The triazolopyridine azo dyestuffs according to the invention are advantageously suited to the dyeing or printing of textile materials. These are, for example, fibers composed of cellulose esters or polyesters, but also of polyamides, or mixed fabrics of polyesters and cellulose fibers. Dyeings or prints having high fastness to dry heat setting and pleating and high brilliance are obtained here. The novel dyestuffs also have a high dyeing power.

To achieve a favorable dyestuff composition, it can be advantageous in some cases to use mixtures of the dyestuffs of the formula I with one another for dyeing.

The triazolopyridine azo dyestuffs according to the invention are furthermore advantageously suited for thermal transfer from a support to a plastic-coated paper by means of an energy source (see e.g. EP-A-416 434).

The following examples will illustrate the invention in greater detail.

EXAMPLE 1

a) Diazotization

15.20 g (0.10 mol) of 4-tert-butylaniline were dissolved with cooling in a mixture of 40 ml of water and 30 g of 35% strength by weight hydrochloric acid, and 100 g of ice were added. 32 g of 23% strength by weight aqueous sodium nitrite solution were added dropwise at from 0° to 5° C. and the mixture was then stirred at from 0° to 5° C. for 3 h.

b) Coupling

5.05 g (0.025 mol) of 4-cyano-2-ethyl-7-hydroxy-5-methyl-1,2,4-triazolo[1,5-a]pyridine were dissolved in a mixture of 10 ml of N-methylpyrrolidone, 30 g of ice, 4 g of 50% strength by weight sodium hydroxide solution and 2 g of sodium hydrogencarbonate and about 100 g of ice were added. The diazonium salt solution described in a) was added dropwise at from 0° to 5° C. in the course of 4 h. The mixture was then stirred for 4 h. After coupling was complete, solid Was filtered off with suction, washed until neutral and dried at 60° C. under reduced pressure. 7.2 g (80% of theory) of the dyestuff of the formula ##STR9## (M.p.: 226°-228° C.; λ_(max) (CH₂ Cl₂): 476 nm)

were obtained, which dyes polyester in a yellow shade.

EXAMPLE 2

a) Diazotization

3.65 g (0.02 mol) of 2-butoxy-5-methylaniline were dissolved in 80 ml of glacial acetic acid/propionic acid (3:1 v/v) and 16 ml of 85% strength by weight sulfuric acid. 10.4 g of nitrosylsulfuric acid (about 42% by weight N₂ O₃) were added dropwise at at most -5° C. and the mixture was then stirred at from -5° to 0° C. for 2 h.

b) Coupling

4.40 g (0.022 mol) of 4-cyano-2-ethyl-7-hydroxy-5-methyl-1,2,4-triazolo[1,5-a]pyridine were dissolved in 90 ml of N-methylpyrrolidone and 100 ml of water, 0.5 g of sulfamic acid and about 400 g of ice were added. The diazonium salt solution described in a) was added dropwise to this solution at from -5° to 0° C., the pH being adjusted to 7.0 using 25% strength by weight sodium hydroxide solution. After coupling was complete, the dyestuff was filtered off at 60° C., washed until neutral and dried at 60° C. under reduced pressure. 3.9 g (50% of theory) of the dyestuff of the formula ##STR10## (M.p.: 206°-210° C.; λ_(max) (CH₂ Cl₂): 505 nm)

were obtained, which dyes polyester in a red shade.

The dyestuffs listed in the following Tables 1 to 3 can be obtained in a similar manner.

                                      TABLE 1                                      __________________________________________________________________________      ##STR11##                                                                                                     Color shade                                    Ex.                 M.p. λmax[nm]                                                                       on                                             No.                                                                               Q.sup.1      Q.sup.2                                                                            [°C.]                                                                        (in CH.sub.2 Cl.sub.2)                                                                polyester                                      __________________________________________________________________________      3 C.sub.6 H.sub.5                                                                             C.sub.2 H.sub.5                                                                    231-232     yellow                                          4                                                                                 ##STR12##   C.sub.2 H.sub.5                                                                    206-207                                                                             476    yellow                                          5                                                                                 ##STR13##   C.sub.2 H.sub.5                                                                    225-226                                                                             476    yellow                                          6                                                                                 ##STR14##   C.sub.2 H.sub.5                                                                    207-208                                                                             478    yellow                                          7                                                                                 ##STR15##   C.sub.2 H.sub.5                                                                    202-203     yellow                                          8                                                                                 ##STR16##   C.sub.2 H.sub.5                                                                    92-93                                                                               476    yellow                                          9                                                                                 ##STR17##   C.sub.2 H.sub.5                                                                    226-227                                                                             488    orange                                         10                                                                                 ##STR18##   C.sub.2 H.sub.5                                                                    236-238                                                                             486    orange                                         11                                                                                 ##STR19##   C.sub.2 H.sub.5                                                                    241-242     orange                                         12                                                                                 ##STR20##   C.sub.2 H.sub.5                                                                    >230 476    orange                                         13                                                                                 ##STR21##   C.sub.2 H.sub.5                                                                    234-235     orange                                         14                                                                                 ##STR22##   C.sub.2 H.sub.5                                                                    260-261                                                                             496    orange                                         15                                                                                 ##STR23##   C.sub.2 H.sub.5                                                                    180-185                                                                             500    red                                            __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR24##                                                                                                          Color shade                               Ex.                      M.p. λmax[nm]                                                                       on                                        No.                                                                               Q.sup.1      Q.sup.2  [°C.]                                                                        (in CH.sub.2 Cl.sub.2)                                                                polyester                                 __________________________________________________________________________     16                                                                                 ##STR25##   CH(CH.sub.3).sub.2                                                                      216-217                                                                             470    yellow                                    17                                                                                 ##STR26##   (CH.sub.2).sub.2 OC.sub.3 H.sub.7                                                            476    yellow                                    18                                                                                 ##STR27##   CH(CH.sub.3).sub.2                                                                      221-222                                                                             476    yellow                                    19                                                                                 ##STR28##   CH(CH.sub.3).sub.2                                                                      196-197                                                                             476    yellow                                    20                                                                                 ##STR29##   CH(CH.sub.3).sub.2                                                                      230-231     yellow                                    21                                                                                 ##STR30##   CH(CH.sub.3).sub.2                                                                      222-223     yellow                                    22                                                                                 ##STR31##   CH(CH.sub.3).sub.2                                                                      225-226                                                                             478    yellow                                    23                                                                                 ##STR32##   (CH.sub.2).sub.2 CO.sub.2 C.sub.4 H.sub.9                                               164-165                                                                             478    yellow                                    24                                                                                 ##STR33##   CH(CH.sub.3).sub.2                                                                      170-171                                                                             476    yellow                                    25                                                                                 ##STR34##   (CH.sub.2).sub.2 CO.sub.2 C.sub.4 H.sub.9                                               176-177                                                                             494    orange                                    26                                                                                 ##STR35##   (CH.sub.2).sub.2 OC.sub.3 H.sub.7                                                       190-191     orange                                    27                                                                                 ##STR36##   CH(CH.sub.3).sub.2                                                                      253-254                                                                             496    orange                                    28                                                                                 ##STR37##   CH(CH.sub.3).sub.2                                                                      240-241     orange                                    29                                                                                 ##STR38##   (CH.sub.2).sub.2 OC.sub.3 H.sub.7                                                       198-200                                                                             510    red                                       30                                                                                 ##STR39##   CH(CH.sub.3).sub.2                                                                       209 502    red                                       31                                                                                 ##STR40##   CH(CH.sub.3).sub.2                                                                      >230 504    red                                       32                                                                                 ##STR41##   (CH.sub.2).sub.2 OC.sub.3 H.sub.7                                                       150-154                                                                             504    red                                       33                                                                                 ##STR42##   (CH.sub.2).sub.2 OC.sub.3 H.sub.7                                                        98-102                                                                             500    red                                       __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR43##                                                                                                          Color shade                               Ex.                      M.p. λmax[nm]                                                                       on                                        No.                                                                               Q.sup.1      Q.sup.2  [°C.]                                                                        (in CH.sub.2 Cl.sub.2)                                                                polyester                                 __________________________________________________________________________     34                                                                                 ##STR44##   C(CH.sub.3).sub.3                                                                       >230 492    orange                                    35                                                                                 ##STR45##   CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                      140-141                                                                             494    orange                                    36                                                                                 ##STR46##   SC.sub.4 H.sub.9                                                                        202-204                                                                             504    red                                       37                                                                                 ##STR47##   (CH.sub.2).sub.5 C(CH.sub.3).sub.3                                                      137-141                                                                             500    red                                       38                                                                                 ##STR48##   C.sub.4 H.sub.9                                                                         >230 502    red                                       39                                                                                 ##STR49##   CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                      158-165                                                                             502    red                                       40                                                                                 ##STR50##   CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                      180-181                                                                             506    red                                       41                                                                                 ##STR51##   C(CH.sub.3).sub.3                                                                       206-209                                                                             498    red                                       42                                                                                 ##STR52##   C(CH.sub.3).sub.3                                                                       219-221                                                                             502    red                                       43                                                                                 ##STR53##   (CH.sub.2).sub.5 C(CH.sub.3).sub.3                                                      120-126                                                                             500    red                                       44                                                                                 ##STR54##   (CH.sub.2).sub.5 C(CH.sub.3).sub.3                                                      124-129                                                                             504    red                                       45                                                                                 ##STR55##   SC.sub.4 H.sub.9                                                                        156-160                                                                             512    bluish-red                                46                                                                                 ##STR56##   SC.sub.4 H.sub.9                                                                        175-178                                                                             516    bluish-red                                47                                                                                 ##STR57##   C.sub.4 H.sub.9                                                                         >230 515    bluish-red                                48                                                                                 ##STR58##   SCH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                     195-197                                                                             525    bluish-red                                __________________________________________________________________________ 

We claim:
 1. A triazolopyridine azo dyestuff of the formula I ##STR59## where A is nitrogen,E is a radical of the formula C--R¹, where R¹ is C₁ -C₂₀ -alkyl, which is unsubstituted or substituted and can be interrupted by 1 to 4 ether oxygen atoms, or is unsubstituted or substituted phenyl, mercapto or unsubstituted or substituted C₁ -C₂₀ -alkylthio, one of the two radicals R² and R⁴ is cyano, carbamoyl, carboxyl or C₁ -C₄ -alkoxycarbonyl and the other is a radical of the formula D--N═N--, where D is a radical of a diazo component from the aniline series, R³ is C₁ -C₄ -alkyl which may also be interrupted by an ether oxygen atom, or phenyl and R⁵ is hydroxyl, mercapto, the radical --NY¹ Y², where Y¹ and Y² are identical or different and independently of one another in each case are hydrogen or C₁ -C₄ -alkyl or, together with the nitrogen atom bonding them, are a 5- or 6-membered saturated heterocyclic radical, or the radical of a CH-acidic compound, with the proviso that if R⁴ is the radical of the formula D--N═N--, the two radicals A and E can also be exchanged for one another.
 2. A triazolopyridine azo dyestuff as claimed in claim 1, wherein one of the two radicals R² and R⁴ is cyano and the other is a radical of the formula D--N═N--, where D has the meaning mentioned in claim
 1. 3. A triazolopyridine azo dyestuff as claimed in claim 1, wherein R² is cyano.
 4. A triazolopyridine azo dyestuff as claimed in claim 1, wherein R³ is C₁ -C₄ -alkyl.
 5. A triazolopyridine azo dyestuff as claimed in claim 1, wherein R¹ is C₁ -C₁₃ -alkyl which may be interrupted by 1 or 2 ether oxygen atoms, or is C₁ -C₁₃ -alkylthio.
 6. A triazolopyridine azo dyestuff as claimed in claim 1, wherein R⁵ is hydroxyl.
 7. A process for dyeing or printing a textile material comprising applying the triazolopyridine azo dyestuff of claim 1 to said textile material. 